New Sales Rep

Finally, I allow you to see the end result and as you stand in my bedroom looking at yourself in my full length mirror you can't believe what you are seeing. As you shift on your heels and touch and feel the changes, you start to realize that you have definitely taken a much bigger step than you had thought. Sensing that you are a bit overwhelmed I tell you to go into the lounge and have a drink while you wait for me to get dressed. As you totter off on you 5" heels, trying to become familiar with their height I smile a very devious smile.

Knowing that our dinner guests will be arriving with in a couple of hours I quickly get dressed in a matching outfit and head to the lounge to see how you are doing. As I enter the lounge you start to come to me to give me a kiss, but I hold you off and tell you that I don't want to smear our lipstick before our guests arrive. This last comment pulls you up short, but before you can ask any further questions the clock in the lounge chimes eight and we can hear the sound of a motor. I tell you to sit and relax and that I will be back. As I reach the aft deck I see a smaller yacht approaching and wave at the handsomely dressed man on the bow.

Once the boats are alongside each other the gentleman steps across and embraces me and gives me a very passionate kiss. As we separate the driver of the yacht emerges from the darkness carrying several containers and starts to hand them over to us. When he is finished he too comes aboard my boat and gives me a peck on the cheek. I lead the two men to the dining room and we quickly layout the food which they brought. We then head into the lounge so you can meet our guests. As we enter you seem lost in your own thoughts, but are quickly brought back to reality as you see two men in tuxedos enter behind me. You rise from the couch and I introduce Tom and Barry to you, and introduce you as Gerry to them. Both men walk over and kiss your hand while greeting you. You are flushed by all this and don't notice that Tom seems to linger as he kisses your hand.

As Tom and you make small talk, I mix drinks for everyone. While I am making the drinks you notice Barry come over behind me and rest his hand on my waist. You feel a slight pang of jealousy, but it quickly fades as Tom's hand brushes against yours and you feel a new feeling inside. I smile at you as I bring the drinks over and you return the smile not sure of what I have planned. You then lean toward me and whisper to me that you need to use the restroom and so I inform the gentlemen that you and I are headed to the ladies room. As we enter the bathroom and I close the door, you become very excited and start demanding what is going on and what am I up to.

I calmly explain that Barry is an old friend of mine who saw that my yacht was not in its slip and radioed me and wanted to know if I would be interested in a visit and some dinner. When I explained I was with someone, he said no problem and that he too would bring someone. I guess he assumed I had a girlfriend with me and that is why he brought Tom. You seem a bit confused and ask why would Barry think you had a girlfriend with you? I explain that I was once married to Barry, but ended up leaving him for another woman.

This statement flabbergasts you. I go on to explain that since then I have realized that I actually like both men and women and that I also have a domineering streak in me. Since our divorce I have kept in touch with Barry and have on occasion shared his bed, sometimes with just him and sometimes with someone else too. All this new information comes as a shock to you and I can see it in your face, so I come over and give you a big hug and lean in to give you a very passionate kiss. As we separate, I tell you that I am very interested in continuing what we have started this weekend and ask you what you want to do. As you turn your head away from me and see our reflection in the mirror, you see two very sexy, very beautiful women and know that you can't go back to how things were before.

Though you never thought of cross dressing you realize that the desire to wear women's clothes and to look sexy has always been a part of who you are. You turn back to me and look me in the eyes and tell me that you are in love with me and that you couldn't imagine your life without me and all that that entails. You then kiss me very passionately. As we break our kiss I tell you to hurry up and pee while I fix my makeup and then I will help you with yours.

As we return to the lounge Barry asks if we are ready for dinner and leads us into the dining room. We enjoy a most wonderful meal with some very good wine that seems to have no end. I notice that initially you keep your distance from Tom, but as the wine flows and the meal progresses your hand seems to drift closer and closer to his and likewise his to yours. At one point I notice that he has his hand on yours and as you reach for your wine glass he nonchalantly drops it o your leg. You don't seem to notice or care in fact you seem rather smitten with all the attention Tom is paying you.

After finishing a wonderful dinner, Barry suggests we head out to the deck to enjoy the night sea air. As we all reach the deck, Barry silently directs me toward one side and Tom leads you to the opposite. As you and Tom lean against the rail he places his hand at the small of your back and begins to lean into you. Without really thinking about it, you lean back and enjoy his closeness and wonder what it would be like to kiss him. As you are thinking this thought Tom leans down and kisses you. You decide to let go of any inhibitions you have and kiss him back. As you continue to make out, Tom's hands begin to roam all over your body. His sensual touches send an electric shock through your body and you feel a stirring in your groin though you don't feel your member seem to respond.

As you wonder about that Tom brushes his fingers across your nipples and all other thoughts are lost. Before you know it Tom has unbuttoned the front of your dress and is flicking his tongue across your nipples, which causes you to swoon, moan and grab his head and pull it closer. He continues to lick and suck your nipples for several minutes and then stands up and gives you a deep, sensual kiss while he kneads your ass with both of his hands. As you break the kiss your hands start to unbutton his tuxedo shirt and as you expose his very muscular chest a gasp escapes your lips. You then proceed to kiss and suck his nipples and feel his hands on your shoulders.

As you continue to kiss his chest he gently pushes your shoulders down and you continue to kiss and nibble until you reach his pants. As you look down at his crotch you notice that he has quite a big bulge and realize that it was you that caused it. Your curiosity gets the better of you and you watch as your hands with red painted fingernails begin to unbuckle his belt and unzip his zipper.

As his pants drop to the deck you can see his member straining to get out of his underwear and he applies more pressure to your shoulders and without thinking about it you drop to your knees and are now face to face with his bulge. You swallow once and decide you have to see his package and so you hook your thumbs into his waistband and pull his underwear down to join his pants. You are now face to face with a very large, very hard penis that seems to have you mesmerized.

You lick your lips again and then lean in and give it a quick kiss. As you rock back you again see a set of red lips on the tip of a cock and feel a stirring in your depths. You then begin to do what you did earlier today and lick his shaft from base to tip. In fact your nose bumps into his ball sack and so you decide to lick and suck that too. As soon as you begin to suck his balls, one at a time, into your mouth, Tom lets out a deep moan and his knees buckle. You reach up grabbing his hips and push him back toward the bench and have him sit down before he falls on top of you.

Once seated you then return your attention to his monster cock. After tonguing his balls and smearing your saliva up and down his shaft you go back to the head and opening your mouth begin to take it in. As you take more and more into your mouth you realize that he is slightly larger than my dildo and you wonder if you will be able to take it all in. It isn't long before you have the majority of his cock in your mouth and down your throat and you have your nose buried in his pubes. By this time Tom has his hands resting on your head and after giving you a couple of minutes he begins to pull your head back.

You snap out of your revelry and without any more encouragement begin to bob back and forth on his cock. In fact something inside you seems to click and you begin to very eagerly suck his cock, so much that your one hand plays with his balls while the other hand encircles the base of his shaft and strokes his member.

Before long you begin to feel his cock start to swell and as you feel the first spurt of his seed hit your throat his hands pull your head forward pushing his cock further down your throat. You quickly begin to swallow his load, however, he cums a lot more than the small amount I gave you earlier today. You try to keep up, but some starts to leak out around his cock past your lips. Finally, he finishes flooding your throat with his cum and starts to soften, as he allows you to slip off of his cock you notice several red rings around it and know that it was your lips that created them. As his semi hard member leaves your mouth, you stretch you jaw and reach up and gather his cum that escaped with your finger and while looking in his eyes lick it clean.

He smiles lovingly at you and pulls you up to his lap and while you sit down making sure your dress flairs out so he has access to beneath it. You lean in and start making out again while his one hand strokes your nylon clad legs and the other strokes and pinches your ass. At one point he shifts you so that he can reach your rosebud and begins to tease you back there. As his finger tip lingers at your opening your body remembers from earlier and the muscles flex and try to grab at his digit. It momentarily disappears but quickly returns, but now has something cool on it. You realize it is lube and so you relax your muscles so he can enter you with the lube and his finger in order to prepare you. He slowly works his finger into you until he is buried up past his second knuckle and then begins to stroke it in and out of you. As he continues to do this the only thing you can think of is having his monster cock filling you.

After letting him probe with his finger for several minutes you stand up and face away from him, lift your dress and begin to lower your primed hole towards his now hard cock. When the tip finally touches your rosebud you feel his hands on your hips and feel him start to pull you down. You relax your muscles and allow your weight to help you impale yourself on his shaft. As his bulbous head slips past your opening you let out a gasp, and slowly continue to lower yourself onto his entire shaft until you are completely nestled against his groin and can't believe how wonderful his huge cock feels filling your backside.

As you sit and enjoy the fullness, he reaches around and begins to pinch and pull at your nipples. His ministrations cause you to wiggle and moan with anticipation. As you feel his cock twitch inside of you, you begin to slowly raise yourself up and then lower yourself back down. At first you take it slowly to allow his monster to stretch you, but soon enough you are frantically riding his cock impaling yourself until you are bottoming out on his groin.

You continue to do this for at least half an hour, enjoying every stroke as you remove and then quickly refill your backside. As your legs begin to tire he reaches around and grabs your 'clitty' and begins to play with it. Due to the lotion I have applied to your groin you can't really feel his hand, however, you can feel a deep rooted stirring deep within you and suddenly the most intense orgasm rips through your body and your deflated penis starts to leak your juice. Just as your orgasm explodes, Tom's monster cock also erupts shooting wad after wad of cum deep into your bowels. As you feel him empty his load inside you, you let out a primal scream and slam your ass all the way down onto his cock and flex your muscles in order to milk every last drop out of his member.

As you both come down from your sexual highs you collapse back against him panting with exertion. He then brings his fingers up to your mouth and feeds you your own cum which you eagerly suck off his fingers until they are clean. As you bask in the afterglow, you notice Barry and I come around the corner. My clothes seem a bit disheveled and you realize that you are not the only one who got lucky. You slowly stand and immediately feel the giant void in your ass.

As I approach I whisper to you to bend at the waist and clean Tom up, which you readily do. As you lick and suck his cock clean of his cum, I come behind you, lift your dress and insert the butt plug from earlier in order to keep his cum inside you. When you are finished you stand up and Tom does too and begins to get dressed. Once he is finished he gives you a very passionate kiss good night and thanks you for a most wonderful time. Barry and Tom give us each a kiss on the cheeks and re-board their yacht and slowly go on their way. As their yacht disappears from sight you turn to me and seem to radiate as we fall into an embrace. It is pretty late and I suggest we go to bed so you can tell me all about your first experience. As we head toward the stateroom you wonder what I have in store for you, but aren't worried because you truly love what you have become.

The End